Moises in the Promised Land

It was the summer of 1984. A few nuns were strolling the streets of La Romana, a resort town in the Dominican Republic, when they heard a baby’s screams coming from a dumpster. The news soon reached the bronzed ears of the city’s most renowned resident, Oscar de la Renta, who at the time was mourning the death of his first wife.

On a recent Thursday afternoon, Moises Oscar de la Renta, now 24, picked me up in a Lincoln Town Car he had hired to run some last-minute errands in preparation for a camping trip he was taking that weekend with two attractive young women. They were headed to a waterfall not far from the de la Renta family compound in Kent, Conn. He was planning to take a great many photographs; he needed to pick up all the proper equipment.

(Yes, he said, he had hooked up with the women in question, Char and Michelle, but this wasn’t going to be that kind of camping trip. “I’m just excited to be in nature and do art,” he said, flashing a big, boyish smile.)

Moises de la Renta currently resides in a spacious, one-bedroom apartment in Manhattan’s Turtle Bay. He spends his days toiling as an assistant designer at his father’s company. He’s developing his own ready-to-wear line, which will bear his initials: MDLR.

“I’m shooting to have it ready sometime next season,” he said. “It’s going to be 12, 15 looks at most.” His father, a self-made man, is not the kind of guy to “throw me a million dollars and say, ‘Do what you want.’”

“I’m just starting off with day dresses,” continued Moises. He has big, brown eyes, eyebrows that leap with excitement, prominent cheekbones and a cheerful, giddy disposition. The day we met he wore khaki pants, black Converse high-tops and a paint spattered T-shirt. A pair of tortoise shell bifocals dangled from his neck. Among his many tattoos is one on his chest that reads, “Rock Life Kill Death.”

He’s quick to point out that until a few years ago, his interest in clothes didn’t extend much beyond the beautiful women wearing them. “I didn’t go to school for it,” he said.

He grew up in quaint Kent the only black kid at the local public school. His best friend was the only Jewish kid. He thinks racism is more the province of previous generations. After the 3 o’clock bell, he didn’t rush home, where it was just Moises, his dad and his mother, New York society fixture Annette Reed. He spent his time playing in the woods, taking pictures, painting and reading: “It was lonely growing up and boring, you know—you’re in the country, in the sticks.”

Berkshire School in Sheffield, Mass., was a lot more fun. He was popular and the girls were amazing, “mad hot German girls.”

When he was 16 he got a fake ID and started coming into the city and going to nightclubs. He was expelled junior year for smoking weed; one of his peers ratted him out. His parents, strict and old-fashioned, sent him to Academy at Swift River, a boarding school for troubled teens in Massachusetts. No drugs, no alcohol, no sex. He resented it—the rest of the kids there had serious problems. He now says he’s grateful: All that therapy forced him to get to know himself so well that he suspects he’ll never have a nervous breakdown.

He eventually graduated from Oxford Academy, an all-boys school in Westbrook, Conn., for students with learning disabilities.

“I had a lot of time to get into other things that I wouldn’t really have a chance to explore if I was focusing on girls—so that was good,” he said. “All that time I would have been flirting with girls, I used on photography, so I can’t complain.”

At 19 he moved to New York City, where women again became a distraction: He lasted two years at Marymount Manhattan College.

“I came here thinking it was going to be 1969—or like the Factory,” he said. “I heard all these stories from my dad and his friends.”

“Now I feel like, everybody goes to the same place, you see the same people,” he said. “I remember when Bungalow was hot, man—you could be sitting next to some good-looking skater kid, Quentin Tarantino on one side, on the other side you’ve got some crazy lady and a homeless guy. As long as you were cool and you looked cool, you got in. Now it’s all about this”—he rubbed imaginary cash between his fingers.

One night three years ago, he met Greer Simpkins, a porcelain-skinned brunette. They began dating and fell in love. Earlier this year, she read Moises’ diary and discovered he’d been unfaithful. “You know how girls are, once they see something like that, they can never get over it,” he said.

(“He has a heart of gold,” Ms. Greer told me. “He loves to cook. He’s a big connoisseur of tea. He’s into botany. You don’t meet too many 24-year-old guys who actually reads about plants and herbs. He likes to listen to vinyl and have tea time.” She added, “He adores his father and takes really good care of him. He goes to visit him on the weekends.”)